Hard-Core Shipping
by Descha05
Summary: Sam is tired of Dean and Castiel not knowing how they feel for each other. He decides to call up Gabriel, but instead of helping Sam, he proposes a challenge. If Gabriel can hook them up first, it means a kiss from Sam. If Sam can hook them up first, he doesn't have to feel annoyed with them every time they're together. Who will win?
1. The Challenge

Sam was getting so tired of the sexual tension between Dean and Castiel. His brother and the Angel didn't seem to feel it, but Sam sure as hell could, and it was starting to get annoying. One particular night, Sam got so tired of the two of them, that he decided to make a call.

Gabriel appeared in front of him before the phone was even close to finished ringing. He smirked and took it, hanging it up before handing it back to Sam. "What's up, Samwich?"

"It's Dean and Cas. They're driving me insane," Sam told him, "I need help getting them together. They don't even know how in love with each other they are, Gabe!"

Gabriel hummed before grinning mischievously. "How about...I don't help you. Instead, we have a little contest to see who can get them together first?"

Sam considered it. "And what happens if you win?"

"If I win, you gotta give me a big ol' kiss on the lips, and if you win, you get the satisfaction of knowing our brothers are finally screwing each other,"

Sam's face screwed up in slight disgust before he nodded his head. "Alright, bring it Gabriel,"

"Oh don't worry, I'll win,"

With that, Gabriel disappeared, leaving Sam alone to come up with a game plan.


	2. Attempt 1

**Attempt #1**

 **Sam**

Sam looked at himself in the mirror and smirked at his handiwork. He had successfully made himself look sick. Now it was time to work somemagic. Sam grabbed a cup of milk and splashed it into the toilet, making gagging noisesvas if he was actually throwing up. There was a knock at the door.

"Hey, Sammy, you okay in there?" Sam grinned. It was Dean. Perfect

Sam opened the door a crack. "I'm sick," he said, making his voice hoarse. "I won't be able to go on the hunt with you, so you'll have to take Cas instead,"

Dean looked behind him and nodded his head. "Alright, where are we going?" He asked, looking back at Sam. Sam pulled out a oieace of paper with an address on it and handed it to him. Dean thanked him and left, telling Cas to gcome with him. Castiel stayed behind and touched Sam's forehead.

"You shouldn't feel sick anymore," he said.

"Thanks, Ca-" but Cas was gone.

Sam grinned. Everything was going perfectly.

* * *

When Dean and Cas arrived at the address, it was an understatement to say that they were surprised. They were parked in front of a big colourful bar with neon signs hanging outside. Dean could hear the music from outside in the Impala. He sighed. Sam really knew where to get the best cases.

Castiel got out of the car first, standing there squinting at the bright lights. Dean patted his back when he got out and went up to the front doors. "Let's go, Cas," he said.

Castiel was hesitant, but he followed Dean anyway. They exchanged a look before opening the door. When they were finally inside, heads turned to look at them. Men turned to look at them. Dean let out a sarcastic laugh.

"What is so funny?" Cas asked, his face scrunched up in confusion and his head tilted to the side.

"Sam sent us to a freaking gay bar!" Dean yelled over the music, "I thought I was gonna get laid tonight, but I guess not," he added jokingly.

There was a look on Castiel's face that he couldn't place, so Dean told him to stay put as he went to get a few drinks for them. He patiently stood by the bar and waited, occasionally glancing back at a very lost looking Castiel. When Dean looked back one final time, he saw a drunk man talking to Cas. Dean watched on as the man suddenly wrapped his arms around the Angel and started slow dancing with him. Dean squinted as the man turned Cas around, leaving Cas's back turned to Dean.

It was ridiculous how jealous he felt, and Cas didn't seem to be resisting. But his jealousy quickly turned to rage when the song changed and the drunk man started grinding on Castiel. Dean stormed over to them, ignoring the bartender when he asked what Dean wanted to drink. When Dean walked up to them, Cas was facing his direction again. His eyes were wide and his expression was almost frantic. Dean growled and tapped the man's shoulder, ready for a fight when the guy turned around and smiled.

"Oh! Sorry, are you two...together?" he asked.

"Uh...y-yeah! Yeah, this is my boyfriend you're hitting on!" Dean exclaimed, wrapping an arm around Castiel's waist and pulling him close.

"Oh I'm sorry! You two look cute together!" the man grinned, winked at them, and stumbled away, finding another man to flirt with.

Dean kept his arm around Cas, whose eyes were still wide. "Come on, let's get out of here," Dean said, guiding them towards the door.

"What about the case...?" Cas asked, his voice seeming far away.

"Screw it, let's just get back to the motel,"

The car ride back was silent, Dean mulling over what happened that night, and Castiel's heart racing.

* * *

Sam had just got out of the shower when the love birds got back from the bar. Dean had barged right in, already yelling at Sam, whereas Cas meekly followed behind him, an awkward expression and a blush on his face.

"What the hell, Sam? There wasn't even a case there!" Dean yelled.

"I thought there was," Sam said, pretending to sound confused.

"Cas got _ground_ on, Sam!" Dean raged, pointing to Castiel, who was now sitting stiffly in a chair.

Sam couldn't help but chuckle slightly. "Sorry, Cas,"

The Angel didn't answer. He merely flicked his eyes around the room, avoiding the brothers' looks.

"Good job, Sam, you freaking broke him!"

Sam sighed and shook his head. That plan had failed, but his next one would work. He would make sure it would.

* * *

 **Gabriel**

A couple of days after the bar incident, Gabriel appeared inside of the Winchester's motel room. The brothers were asleep at the moment, leaving him to stand over Dean's bed against the wall. He had made sure that he was invisible to both Angels and Humans alike before arriving. His plan? Get Castiel in the same bed as Dean Winchester. Only, Castiel wasn't there at the moment. Gabriel looked around the room again. Still no Castiel. Frowning, he placed a finger on Dean's forehead and made him call out to the Angel.

Not even a second passed before Castiel was standing in front of Dean's bed. Dean was awake now, and about to get up when he found that he _couldn't_.

"Dean?" Castiel asked, tilting his head.

"I can't move, Cas," Dean said, seeming to struggle under an invisible weight.

"What do you mean?"

"I don't know! Just help me up, man!"

Castiel awkwardly took Dean's hand and tried to pull him up, but he found he couldn't. He pulled and flapped his wings, and yet, he still couldn't pull the hunter out of the bed. Castiel, slightly winded now, stopped pulling, and leaned in to see if he could get a better understanding of what was happening. All of a sudden, he was forcefully pushed forward. He toppled over the bed and landed on top of Dean with an 'oof'.

"Jesus, Cas," Dean muttered, "what the hell are you doing?"

"Something pushed me,"

"What? How?"

"Or maybe I just lost my balance..."

Dean chuckled. "Does that even happen to Angels?"

Cas smiled at him. "I didn't think so,"

Behind them, an invisible Gabriel grinned. He was going to win this challenge, he knew it. His moment of glory was shattered when Sam cleared his throat.

"This is interesting," He mused. Gabriel face palmed. Why did Sam have to get in the way?

Dean panicked and pushed Cas off of the bed, resulting in a thump and a noise of surprise. He winced and apologized to the Angel before turning back to his brother. "Cas was just trying to help me. I couldn't move for a sec," Dean explained hurriedly, "then he lost his balance and fell on top of me,"

Sam raised an eyebrow as Castiel groaned and stood. "It's true, Sam," the Angel said gruffly, "I was just helping your brother,"

"Right, whatever," Sam smirked and got up to make coffee. Gabriel made sure he didn't have any filters before leaving, already coming up with another plan. One that would definitely work.


	3. Attempt 2

**Attempt #2**

 **Gabriel**

His next plan is so simple, he's almost reluctant to conduct it. He wanted to give Sam more of a fighting chance. It only seemed fair since he was merely a human. An adorable, smart, Sasquatch-like human, but a mere human nonetheless. So he stayed with the Winchesters, letting time go by for Sam to think of his next move. Gabriel could tell the hunter had nothing planned yet. Or maybe he was waiting for Gabriel to strike first? He shrugged to himself as the Winchester brothers finally fell asleep. His eyes were set on Castiel, and he knew his little brother would hate him if he ever found out that Gabriel was the one who did this to him.

With a small smirk, Gabriel walked up to Castiel and held his hand up. "Sorry little bro," he murmured. He snapped his fingers and Cas fell asleep.

Not only was he asleep however. His vessel had also mysteriously turned into a beautiful woman. Gabe grinned to himself, proud of his handiwork. He had to say, Castiel looked absolutely _stunning_ in his new female body. He was sure Dean would love it, and hopefully he would reveal his true feelings this way. It would be easier for him to say how he felt while Cas was a female instead of having to admit he was Bisexual.

Smiling to himself, he turned to walk out of the room. But something stopped him. Sam's cute, peaceful face. Sighing, Gabriel pulled an IPod and an AUX cord out of his pocket and quickly scribbled a note to attach it to. He placed it on the nightstand beside Sam and woke him up before poof-ing out of the motel. He wouldn't stray too far, however. He wanted to see how all of this played out.

* * *

 **Sam**

Sam woke with a start to find it only being an hour from when he first fell asleep. Sighing, he went to turn on the light when something stopped him. There was an IPod and some sort of cord on the nightstand. He turned on the light and read the note that was taped to it.

 _Dear Sammy,_

 _I thought you could use a bit of a boost. You seem to be thinking a little too hard about this. Anyway, plug this into the Impala and play it. I made sure to put an actual AUX plug in into the car. Oh and also, I turned Castiel into a woman._

Sam stopped reading for a moment in shock before looking over where Cas was. Sam blinked in surprise. There was a woman wearing the same outfit Cas had. So Cas was a girl now? He shook his head and kept reading.

 _Don't be alarmed if he doesn't wake up in the morning. Take advantage of it! The IPod has love songs on it. Maybe it'll help Dean pour out his feelings or something._

 _Love, Gabriel_

Sam rolled his eyes, a blush forming on his cheeks. He looked back over at the slumbering Cas and instantly had an idea. Smirking, he turned the light back off, put the device and the cord under his pillow, and settled back into bed, his plan forming even as he slept.

The next morning, Sam was shaken awake by a panicked Dean. "What? What's wrong?!" Sam asked, sitting up.

"It's Cas, dude!" Dean yelled, "He's unconscious...and he's a _she_!"

"What...?" Sam asked, playing dumb.

"Look, Sam!" Dean pointed to Cas, who was still slumped awkwardly against the wall. His - er, _her_ hair was long and wavy. It was raven black, and her skin was un-blemished and perfect. Sam shook his head. Gabriel really made Cas an attractive lady.

"Okay, okay, just calm down," Sam said, standing. "Take him - _her_ into the backseat of the Impala and stay back there with her. She might not know what's happening, so it's best if I drive and you stay in the back with her so she sees a familiar face when she wakes up,"

Surprisingly, Dean didn't object. He just nodded his head and went over to Cas. He gently picked her up bridal style and walked out the door with her. Sam got dressed and stuffed the IPod into his pocket. He packed up all of their things and hurried outside. Dean was already in the back with Cas, awkwardly sitting with her head on his shoulder.

Sam quickly put everything in the trunk and hopped into the driver's seat. "Alright," he muttered to himself, taking out the IPod. Despite Dean's protests, Sam plugged it in and hit shuffle. He smirked and drove out of the parking lot. He ignored Dean's complaints when the song finally came on.

 _"You see this guy, this guy's in love with you._ _Yes I'm in love, who looks at you the way I do?"_

"Turn this shit off, Sam!" Dean yelled from the back.

"Wasn't it you that said the driver picks the music?" Sam asked, smirking at him from the rear-view mirror. Dean was quiet, only mumbling his complaints to a still unconscious Castiel.

The next song made Sam cringe, but he would withstand it for the sake of Dean and Cas's relationship.

"Oh come on, Sam! Celine Dione?!" Dean yelled. Sam was about to snap at him when Castiel let out a small groan. Her eyes fluttered open, and Sam was satisfied to see Dean's eyes widely fixated on hers.

"D-dean?" Castiel's voice was like - well, the voice of an Angel. "W-why is...why is my voice so high and...why is this song playing?"

"Cas," Dean was grinning widely. "You're awake,"

"Yes..." Castiel looked troubled. That's when she started looking herself over. She grabbed her breasts. "Those are new," she muttered.

Sam burst out laughing while Dean only awkwardly took Cas's hands off of herself. She narrowed her eyes and tilted her head. Dean cleared his throat. "Do you know how you ended up a...a chick, Cas,"

"I'm not a baby bird," Castiel said, blinking at Dean.

"Ah, yeah, I get that," Dean rolled his eyes, "I mean a woman. Why are you a woman?"

"Oh it happens all the time," Cas said, "to Angels in general, I mean. Not to me. This is my first time accidentally switching genders,"

"Angels accidentally switch genders?" Sam asked as the song changed. This time it was Paul McCartney.

"Sometimes, yes. Angels don't actually have genders. Sometime's we accidentally...switch our vessel's gender," Castiel answered, cocking her ear towards the speaker at the back. "This song is more enjoyable than the other one," she murmured. Dean coughed, causing Cas to look over at Sam. "No offense, Sam,"

"None taken,"

* * *

That night they settled into a quiet little motel with two beds, as per usual. Dean was bored and restless, and he really needed something to help cope with the fact that Cas was a female. An _attractive_ female at that. So he rounded up the Angel and his brother and made them go to a bar with him. He didn't feel like drinking out alone, and besides, Sam and Cas needed to loosen up a bit.

When they got there, Dean instantly regretted taking Cas. Everyone stared at her, men and women alike. They were all attracted to her, and for some reason that made Dean angry.

 _Since when have I felt like this about Cas getting checked out?_

He thought about the gay bar incident a few days ago. He had felt the same way when that man was grinding against Cas. What was his deal? Shaking his head, Dean went to go get the three of them some drinks. When he returned, he couldn't help but notice Castiel looking extremely uncomfortable.

"Cas? What's up?" He asked, feeling concerned.

"Those men..." Cas said, gesturing behind Dean. "They keep staring at my chest...and they're making inappropriate comments,"

Dean felt a flash of anger, but he forcefully cooled it down. "Just ignore them, they're assholes,"

"Yeah, I wouldn't worry about it," Sam reassured her.

Nodding uneasily, she turned to one of the beers Dean had put on the table and took a drink from it. Everything was okay for a few moments, until one of the men Cas was talking about got up and walked over to them. He slammed a hand down on their table and faced Cas, leaning on the table and blocking Dean.

"What's yer name, pretty lady?"

"Castiel,"

"What a pretty name," the man seemed to lean closer to Cas. Sam and Dean glanced at each other with worried expressions on their faces. The man must have done something, for Cas let out a small sound of distress. Dean stood turned the man around to face him.

"Why don't you back off and leave her alone?" He asked lowly, rage burning in his eyes.

"C'mon, we were just having some fun," the man said, turning back to Cas. "Right, baby cakes?" he winked at her before turning back to Dean.

"I'm warning you, pal."

"Fine, fine," the man put his hands up and backed away from them in surrender.

"C'mon guys, we'll just go buy some drinks from the liquor store," Dean said, staying at Cas's side as they started to leave.

"Thank you D-" Cas was stopped when the same man slapped her ass and wolf whistled. Cas jumped and grabbed onto Dean's arm, turning around to face the man. Before she could go over and smite him, Dean stopped her.

"Let me handle this," he said.

Dean calmly walked up to the man and punched him in the face, sending him falling to the ground. The whole bar gasped in unison, craning their necks to see the fight. The man got up and charged him, but Dean was quick, and he dodged, causing the pig to run into a nearby table. While he was dazed, Dean grabbed the back of his shirt and threw him to the ground again. He started wailing on him until the man plead for him to stop.

"You never, _ever_ treat a woman like that again, you hear me?" Dean yelled.

The man whimpered and nodded his head. Cheers erupted from most of the bar as Dean gently took Cas's arm and led her out of the bar. He didn't notice Sam's proud look, or Cas's look of amazement. He simply led them to the Impala. As he promised, Dean stopped at a nearby liquor store and bought them some booze. Dean and surprisingly, Cas, got drunk that night and fell asleep beside each other on the small sofa in the room. Sam stayed up and watched them for awhile before starting to get undressed so he could sleep as well.

Right when he was about to take his pants off, Gabriel appeared, a smug look on his face. "Aw c'mon, Sammy," he teased, "we aren't ready for third base yet,"

"Sh-shut up, Gabe!" Sam hissed. "What do you want?"

"I just came to make Castiel a man again,"

"Why? I think your plan is working,"

"It isn't. It's going nowhere," Gabriel shrugged and snapped his fingers. Suddenly, Cas was himself again. Very male, and...very close to almost cuddling with Dean.

"Okay, so that's it?" Sam asked.

"Yep. Did you like the songs?"

"Yeah they were uh...interesting,"

Gabriel lightly patted Sam's cheek and winked before disappearing. Sam shook his head and finally got into bed. He closed his eyes and wondered what his next course of action should be.


	4. Attempt 3

**Attempt #3**

 **Sam**

"Cas, what the Hell?!"

Sam woke to find Dean trapped under a sleeping Cas, who was peacefully laying on Dean's lap. Sam let out a small 'aww', earning a death glare from his older brother.

"Come on, Dean, just leave him alone," Sam said, "he's probably tired from switching genders,"

Dean frowned and looked down at the slumbering Angel. He sighed and nodded his head, oblivious to Sam's look of realization.

 _If I manage to keep Cas asleep, maybe Dean will realize how cute he looks._

Sam excused himself, saying he had to go for a walk. He went outside and walked around the motel, stopping behind it. He sighed and looked around. "Hey Gabe, I need your help,"

Gabriel appeared in front of him, a smug smile on his face. "This is war, Sammy. You don't ask your opponent for help,"

Sam rolled his eyes. "Okay, first of all, this is nowhere close to war," Sam said, "secondly, I want to make a deal with you,"

"A deal? Deals are for demons, Sam," Gabe chuckled, "but I suppose I'll hear you out..."

Sam proposed his deal. A sleeping Cas for all the candy Gabe wanted. It was almost scary how fast Gabriel had agreed to these terms. He snapped his fingers, and they were instantly in a candy store.

"Did you do it?" Sam asked a distracted Gabe.

"Yeah, yeah of course,"

"Go nuts then,"

Gabriel grinned and grabbed at least one of everything in the store. He had at least four baskets full of candy. It was safe to say he and Sam had officially become their favourite costumers. When they walked out of the door, Gabriel giddily hanging on to his _very_ large plastic bag filled with candy, they were back at the motel. Gabriel smiled and handed Sam a heart-shaped lollipop before disappearing.

When Sam got back to the room, he was surprised to find Dean staring down at Cas with a soft expression on his face. He cleared his throat to announce his presence, causing Dean to jump and Cas to groan in his sleep. Dean glared at Sam. "You almost woke him up," he whispered harshly.

"Sorry," Sam whispered back. He quietly sat on the edge of his bed and got out his laptop, pretending that he wasn't watching how Dean reacted with Cas. Sam couldn't help but smile, for whenever Dean tried to move, Cas would whine and grumble in his sleep. Dean wouldn't freak out or anything. He would simply move back to the position he was in and murmur something to the Angel in reassurance.

"He looks really peaceful, doesn't he?" Sam asked quietly.

Dean didn't reply. He merely grunted as if he didn't know what Sam was talking about. But Sam caught a small smile on his face. A tender glance down at the Angel. Sam shook his head. His brother was so smitten. It was a shame he hadn't realized it yet. It was also a shame that Sam knew he wouldn't be the one to help him realize it. He was pretty much losing this challenge. He had help from Gabriel on two different occasions. The Arch-Angel was going to win. Sam sighed. It wasn't like it was a bad thing. He really wanted Dean and Castiel to be together, and to be completely honest, he didn't think having to kiss Gabriel was _that_ bad.

"Alright Cas, I gotta move you for a bit,"

Sam was pulled out of his thoughts when he heard Dean softly speak to the Angel on his lap. Sam smiled as Dean gently moved Cas and got up. After gently putting Cas back down on the sofa, he went into the bathroom and shut the door. Everything seemed perfectly fine until Cas started talking in a different language. Sam tilted his head. It must be Enochian. That's when things seemed...off. There was suddenly a kitten in the middle of the room. It meowed and padded over to Sam, looking up at him expectantly. Curious, Sam picked it up and put it on his lap.

Cas said something else, and suddenly, there was a large, fuzzy bumblebee flying around the room. Sam looked at it wearily, not trusting it. He glanced over at the door. "Dean!" He yelled.

Dean opened the door and instantly shut it again at the sight of the large bee. "What the hell is going on, Sam?!" He yelled from behind the door.

Castiel spoke again, making a fuzzy baby bunny appear. It looked at Sam and wriggled it's nose. Sam looked back at the door. "It's Castiel. He seems to be...er...sleep-creating...?"

"What the hell is that supposed to mean?"

"It means, he's creating cute creatures while he's sleeping," Sam glanced at the bee again, who was moving towards the window. "Well, at least things he thinks are cute,"

"What do we do?" Dean asked, cracking the door open.

"I don't know," Sam said. He thought about it. Maybe if Dean sat with him again? "Dean, go sit with his head on your lap again,"

"What, wh-"

"Just do it!"

Grumbling, Dean quietly walked over and gently lifted Cas. He took his earlier position. Cas's head resting comfortably on his lap and Dean's hand at his hair. Much to their relief, the creations had stopped. Sam opened the window to let the bee out. He looked over helplessly at the bunny and the cat. What were they going to do with them?

He decided he would have to give Gabriel another call.

Sighing, he stood and left the room again, the kitten in his arms. It seemed to grow on him, and knowing Cas, he would want to keep the kitten too. He stood outside of the motel and looked up at the sky. "Gabe. Get your ass over here,"

"Ooo, someone's a little feisty!"

Sam gave Gabriel the best glare he could muster, causing the Angel to take a step backwards. "W-what's up, Sammy-o?"

"You know what's up," Sam replied, rolling his eyes. "Wake Cas up. This is going nowhere,"

"I'm making him show you things in his dreams," Gabriel said, "sooner or later, he's going to dream up a Dean,"

"I don't care, Gabe," Sam said, "just wake him up and get rid of his large bumblebee and that adorable bunny,"

"What about the c-"

"We're keeping the cat!"

Gabriel held his hands up in defense. "Okay, okay," he snapped his fingers and disappeared. Sam sighed in relief and looked down at the kitten, who meowed up at him. When Sam returned to the room, he was beyond relieved to find the bunny gone. Castiel however, was still asleep. Or wait...

Sam squinted in amusement. Castiel was obviously faking his slumbering state at the moment. Sam was surprised Dean hadn't noticed, but then again, his older brother was too caught up in playing with Cas's hair. Sam chuckled, going back over to the bed. He put the kitten back down and smiled as it walked over and meowed at Dean.

Suddenly, Castiel was sitting upright and gasping.

"Cas?" Dean asked, panic in his voice. "What's..." He stopped speaking when Cas picked up the kitten and put it in his lap.

"It's so adorable, Dean! Don't you think?" Cas asked, holding up the kitten and looking at Dean with wide eyes.

Sam could tell Dean didn't care to much for the cat, so he coughed and sent Dean a look that said _just agree with him!_

"Er...y-yeah, Cas. He's a cutie," Dean agreed, practically melting at the sight of Castiel's bright, happy smile.

Sam shook his head. He hoped this contest was over soon. As much as he hated to admit it, Sam would actually enjoy it if they acted all lovey-dovey towards each other. He just wondered what Gabriel had planned next, and hoped that it would be enough to win.

* * *

 **Gabriel**

After helping Sam out, Gabriel really had to think of a good, solid plan. A plan that no one would see coming. A plan so great, he would win this contest and finally get to make ou - er - kiss Sam.

Unfortunately, Gabriel didn't have such a plan.

So, the trickster decided whatever he thought up first would be his grand plan. Aha! A musical! Only, Dean was the only one in it. Dean would be the only one to burst into songs that represented his feelings. It would be a pretty depressing musical, but it would also be fun.

Stuffing a chocolate bar in his mouth, Gabriel clapped his hands and disappeared, reappearing in the motel the Winchesters were staying at. The first thing he noticed was that Cas and Sam were gone. He frowned and cocked his ear, hearing voices down the hall outside of the room. When he appeared in the hallway, he saw Cas and Sam talking.

"I know what you and Gabriel are doing, and I'm grateful for your help," Castiel said.

"Aww, thanks kiddo!" Gabriel ruffled Castiel's hair, earning a punch in the face.

"Sorry, it's a reflex," Cas apologized to his brother, who was rubbing his face with a sour expression.

"What are you doing here, Gabe?" Sam asked, sending him bitchface #467.

Gabriel smiled. "Conducting my next plan," he said. He turned to Cas. "You just have to make sure you're with him at all times. He's going to express his feelings with song, so eventually he'll sing a song about you!"

Castiel looked extremely confused, but he seemed to agree anyway. "I will see what I can do,"

"Excellent! Have fun!" With that, Gabriel turned himself invisible again and went to go check on Dean.

Perfect. He was already singing a song about beer.

This was going to be fun.

* * *

It was strange. Very strange. Dean had just got up to get a beer, when all of a sudden he was singing about why he drinks beer.

Dean Winchester does _not_ sing.

He kept telling himself that, but every time he did another line of song would leave him.

Suddenly, just as his beer song had ended, Sam and Cas entered the room. "Oh thank god!" Dean exclaimed. "You need to help me! I've turned into a walking musical number here!"

Sam and Cas exchanged glances before starting to laugh at him.

"This isn't funny!" Dean yelled.

"Sorry man, but you singing in general is hilarious," Sam chuckled.

"Do you think I chose this?" Dean started singing again. He clapped a hand over his mouth to try to stop it, but Dean and Cas could still hear what he was singing. Something about how he didn't choose to sing, which then turned into how he didn't choose this life. It was like a Disney song, only more depressing...and...wait, did he hear musical accompaniment?

Sam burst out laughing as depressing piano played from an unknown source. Even Castiel smiled in amusement, but he tried to restrain it. The music changed as he looked at Cas. A ballad-like guitar strummed in the background. Castiel squinted at him, that small, amused smile seeming to widen.

"Oh come, on!" Dean exclaimed, looking up at the ceiling. He looked back down and at Cas. He clenched his jaw, trying to stop the next song, but he couldn't. For some reason he felt compelled to sing.

 _"When I look at you, I feel a little blue, because you don't know what I do,"_

Castiel's brilliant blue eyes widened considerably. He had confusion with a hint of nervousness in his gaze.

 _"You see, I don't like to talk about my feelings, but I know I should at least tell you,"_

Sam gasped and held his hand over his mouth. This was it. This was a confession of undying love.

 _"You're the best Angel I have ever met. You're the best friend I have ever had. I know it sounds cheesy, but it's true. We're the best of friends, me and you,"_

Castiel looked as disappointed as Sam felt, but the Angel managed a tight smile and a soft thank you. Sam sighed almost sadly and tuned out the rest of Dean's song. He kept glancing at Castiel, making sure the Angel was okay. Sam felt bad for the Angel. He must've thought the same thing Sam had. To find out Dean only thought of them as 'best friends' must have been a pretty hard blow.

When Dean was done, he made them all swear never to mention anything about this ever again. Sam huffed and stood. "I'm going to go salt and burn this ghost's bones. It's almost dark,"

"I'll go as well," Castiel said awkwardly, "Dean, I'm sorry but you should stay here. I don't think the ghost would appreciate your singing,"

Dean huffed and sat down on the bed, grudgingly agreeing. Before Sam could even open the door, they disappeared from the room, leaving Dean alone to sing to himself.

* * *

Castiel distracted the spirit while Sam salted its bones and poured gasoline on it. In mere seconds, the ghost was gone, burned up and evaporated. Cas helped Sam refill the grave when the fire died, talking to him the whole time.

"Why did Dean only say that I was his friend?" Castiel asked when the grave was filled. "I already know that we are friends,"

"I don't know Cas," Sam replied honestly.

"I don't understand," Cas said, flying them to their hallway of the motel. "Are you certain he feels the same w-"

Sam waited for him to go on, but when he looked ahead, he knew why Cas had stopped. Dean was standing in the doorway, clearly flirting with a short blonde girl. He brushed a stray hair out of her face and laughed with her over something. Sam looked over at Cas, wincing. "You okay?" he asked softly.

Castiel's eyes were filled with tears. "I have to go," his voice wavered, and before Sam could stop him, he had swiftly walked passed the girl Dean was flirting with, gently grazed her temple with his index finger, and disappeared. The girl fainted and Dean caught her before she hit the ground. She was awake a few moments after that, and accused Dean of trying to kidnap her.

Dean grumbled in annoyance when the two brothers were finally in the room together. "I was about to get laid tonight, Sammy!"

"I don't really care, Dean," Sam glared at him.

"What's up with you?" Dean asked, "and what was up with Cas? He just...disappeared..."

"He wanted some time alone," Sam replied tensely, "or rather, time away from _you_. Goodnight,"

Dean felt hurt. Why would Cas want time away from him? He shook his head and decided to head to bed himself.

But for some reason, there was a burning sensation of guilt in his chest. "What did I do, Cas?" he asked.

Dean expected the Angel to appear at his bed and tell him what troubled him. But there was nothing. Dean sighed and turned, falling asleep a few moments later.

Little did he know, a very angry Gabriel was watching him, a red eyed Castiel wrapped up in his golden wings.

* * *

 **I'm really sorry I turned it from fun to feelsy** **_;**


	5. Let's Call It Off

**Let's Call It Off**

Gabriel and Sam met in an alleyway a few days after the incident. They had to work something out to get Cas talking to Dean again. After all, they started this mess, so they might as well try to fix it. Dean had been non-stop praying to Cas, trying to get some sort of answer out of him. According to Gabriel, every time Dean would pray, Castiel would pace around Gabriel's house, getting all worked up over whether he should go or not. To be very honest, Gabriel could care less about the older Winchester now. He had hurt his little brother, and that was unforgiving. But Sam wanted them to make up, so Gabriel had to do something about it. He never could resist Sam's puppy dog eyes.

"Let's call off the challenge," Sam said, stuffing his hands in his pockets. "Just until our brothers become friends again," Gabriel was disappointed, but he nodded his head anyway.

"How do we do this?" Gabriel finally asked after a moment of silence.

"We should at least get them in the same room together. But I don't know how Castiel will react, so that might not be the best plan,"

"I think he'll be fine. He's already contemplated visiting Dean about a billion times," Gabriel gave Sam a small reassuring smile. "We'll meet you in the motel some time,"

Before Sam could say another word, Gabriel was gone. Sam sighed and turned around, walking back to the motel to wait.

* * *

It took some time, but Gabriel finally convinced Castiel to go see Dean.

"What if he doesn't want to see me anymore?" Cas asked just as they were about to go, "and what if he hates me now?"

Gabriel sighed and gently grabbed Castiel's shoulders. "Listen, Dean has been praying for you for the past few days right? Would he do that if he didn't want to see you?"

"Well maybe-"

Cas couldn't finish his sentence, for they were already in the middle of Sam and Dean's motel room. Cas kept himself at a distance as Dean stood in surprise.

"Cas, what the hell? Where were you?"

Castiel opened his mouth to apologize, but was cut off by Gabriel. "You owe an apology to my brother, Winchester,"

"What? Why?" Dean looked genuinely confused.

"You know why," Gabriel replied, glaring at him. When Dean gave him a look, he rolled his eyes. "You're so blind!"

"What the hell are you-"

"Shut up and listen for once,"

"Gabriel, I think that is enough," Castiel grabbed his arm and sent Dean an apologetic look.

Gabriel looked back at him and sighed. "Fine. You're lucky, Winchester." And with that, he disappeared.

Dean moved his mouth, but no sound came out. Cas groaned. "Gabriel made you mute," he said.

Dean looked like he should be yelling. He realized it was no use and got up to grab some paper and a pen. _Why the hell would he do that?_

Castiel's eyes shifted, like he would rather not answer the question. But he answered nonetheless. "He must think you talk too much,"

Dean crossed his arms, a small pout on his face. _I don't talk that much!_

"Not according to Gabriel," Cas shrugged and awkwardly avoided Dean's gaze. The tension in the room was going to make Castiel choke. He had never felt so conflicted. Part of him wanted to forgive Dean and have things go back to the way they were, but another part of him just wished Dean would stay out of his life.

He knew he could never allow the latter. So he had to forgive the oldest Winchester, but right now, he really couldn't bring himself to. After all, Dean didn't like him that way. He was always going to pick a girl over him, and every time, Cas would feel hurt. Maybe he didn't really have a place in Dean's life after all.

Castiel had never felt more relieved when Sam walked into the room.

"Castiel," Sam greeted, an unasked question in his gaze as he looked around the room. He set a large paper bag on the table. _Where's Gabriel?_

Cas jerked his head as if to say that he left. Sam seemed to understand and nodded his head. Their attention was turned towards Dean, who was banging his pen against the bedpost. When he was satisfied that he was being given attention, he held up his paper. _Since when were you two telepathic?_

"Since when did you stop talking?" Sam countered, his expression on the verge of a bitchface.

"Gabriel got upset and made him mute," Cas explained.

Sam smirked at Dean in amusement. "I'll be sure to thank him for that,"

Dean gave him the middle finger before turning his back on them. Sam grinned at Cas, who couldn't help but smile. He appreciated Sam helping him, but the Angel still felt off. He felt like he needed to tell Dean how he felt, but then again, he also feared being rejected. Suddenly in a bad mood, Cas sighed and slumped his shoulders. Sam patted his back before turning back to the bag. He ripped it open to reveal three different Styrofoam containers.

"I got Dean two burgers, so you can have one of them," Sam said, handing him a container and giving him an apologetic look.

"Thank you, Sam," Cas didn't have to eat, but since it was offered to him, he opened the container and picked up the burger, avoiding Dean's gaze as he walked over and grabbed his own container. He could see Dean looking at him, so he took a large bite out of the burger to distract himself. The room was dead silent as the three of them ate. Cas kept his head down, knowing Dean was looking at him. When he was done eating, he finally gave in. He looked up and saw amusement on Dean's face.

He pointed to his cheek. Castiel shook his head. "There is nothing there,"

Dean rolled his eyes and pointed to Cas's cheek. Cas wiped at his face, but there was still nothing there. Dean finally leaned over and wiped his face with his hand, smiling when he was finished. He then picked up his paper and started writing again. _I'm not sure what I did, but I'm sorry. Are we friends?_

Cas smiled tightly. "Yes, of course. Friends. Just friends,"

Sam cleared his throat and cleaned up the room to keep out of the awkward situation.

"Grea - oh thank god, I can talk again!" Dean exclaimed.

"Gabriel must have taken pity on you since you apologized," Castiel didn't think it lasted long enough, but he wasn't going to say anything about it.

"Awesome. Hey uh, Cas," Dean looked hesitant, "why was Gabriel so angry at me?"

Cas sighed, his heart in his throat. "D-Dean, look, I-" he cut himself off, looking at his hands. "I just got upset the other night,"

"Why?"

"It's...look, if I tell you, we won't be friends anymore,"

"Cas..." Sam started, stopping when Castiel put a hand up.

"I should tell him, Sam," Castiel said softly, "if he hates me for it...then I will just have to find a way to become friends with him again,"

"Why would I...Cas, what's going on, man?" Dean had a hint of worry in his voice.

"Dean, I love you," Castiel finally confessed, looking right at him.

To say the least, Dean was stunned. He had no idea how to reply to that. "You mean in a...brotherly way, right?"

Cas cleared his throat, still avoiding Dean's gaze. "No...er...romantically," he stuttered. Cas wearily looked up at Dean, not completely surprised to find him looking over at Sam for help. "I'm sorry," Cas apologized.

Dean didn't reply. He stood and walked over to the window, his back to Castiel. "I think you should go, Cas," he finally said, his voice low.

"Go?" Cas asked, "you don't want me around?"

"I just need to think! Go!" Dean yelled. He rubbed his eyes and turned around, not at all satisfied at the empty space where Cas used to be. He looked over to see Sam giving him a glare.

"You just blew it, Dean," He said, shaking his head. "Cas is a good guy who loves and cares about you. I know you feel the same way. Yet you pushed him away. What for, Dean? Your reputation?"

Dean scoffed and gave Sam the cold shoulder. When he turned he found himself face to face with Gabriel.

"So you rejected Cassie, huh?" The Arch-Angel suddenly looked more intimidating than before. "I was right. You really are blind,"

"What, so the both of you are ganging up on me?" Dean asked, "is that what this is?"

Sam sighed and walked over to his brother. "No, Dean. We're just trying to get you to realize how you feel for Cas,"

Dean groaned and sat on one of the beds. "I don't know how I feel about this, okay?" He looked up at the both of them and shrugged. "I like girls, but I also really like Cas. It's just gonna end badly if I enter a relationship with him,"

"Or it could be amazing! Dean, I've seen the way you look at him! You've never looked at any of your girlfriends like that," Sam pointed out, sitting beside him. "Maybe it'll be good for you,"

"Just think about how you feel when you're around him," Gabriel said, "then you'll know for sure,"

Dean fell silent, thinking about all the good times he's had with Cas. What was he doing? He freaking loved everything about that Angel. How innocent he seemed, how peaceful he looked when asleep, how he always had Dean's back no matter what, and not to mention those brilliantly blue eyes. Castiel was amazing. Sam was right, he really did blow it.

Dean groaned and put his head in his hands. "You're right," he said, angry with himself. "I love Cas,"

Sam and Gabriel smiled at each other. "Let me go check on him and then you can apologize," Gabriel disappeared, leaving the two Winchester brothers alone. They sat in silence for a moment before Dean suddenly felt very worried.

"What if he doesn't forgive me?"

"This is Cas we're talking about, Dean. No matter what,he'll forgive you,"

Dean nodded his head, but he still couldn't help but feel worried. He just hoped that wasn't the last time he would talk to Cas. He wouldn't know what to do if it was.


	6. It's Only Love

**It's Only Love**

Dean anxiously waited two days before Gabriel reappeared without Cas and a troubled look on his face. It only made Dean feel worse.

"He doesn't want to talk to you," Gabriel said, "he said it would be better if he left you alone,"

Dean stood from his seat. "Take me to him," he insisted, "I need to talk to him,"

Gabriel looked at Sam, who was now standing beside Dean. He sighed and grabbed onto one of their shoulders each. In seconds they were in the living room of a very nice house. Gabriel looked at Dean as if to tell him to go find Cas himself before sitting down and pulling a half eaten chocolate bar out of his pocket. Dean rolled his eyes and left the room, catching himself chewing his lip in nervousness. He was starting to rethink coming here to talk to Cas, but he really did owe it to the Angel. Dean had been nothing but an ass the past week or so. He really needed to apologize and make it up to him.

The first door Dean opened was surprisingly where Cas was. The Angel was sitting on the bed, reading some sort of book about science and space. He didn't look up from the book, only shifting his reading position every so often. He didn't even look up when Dean entered the room. He only let out a gruff "I'm busy,"

Dean sat down on the bed beside Cas, who instantly turned away from him. Dean would have laughed at how childish it was under different circumstances. "Listen Cas, I've spent a few days thinking and..." Dean paused slightly, "...and I realize that I was a complete asshole to you,"

Castiel slowly lowered the book, only his eyes showing over the old cover. "Go on," he said.

"I shouldn't have flirted with that lady. If I would've known-"

Cas cut him off, his book now forgotten on the bed. "You still would have tried to have sex with her because you obviously liked her,"

"Cas that's not what I-"

"Really? Are you sure Dean? If you're lying to me to try to make me feel better you're only making it worse,"

"I'm not lying, Cas!"

Castiel abruptly stood and turned his back on Dean. "I have decided that it would be best if I leave you alone. I'm just causing unnecessary distress,"

Dean shook his head and stood, grabbing Cas's arm and turning him back around. "We can work this out! You don't have to leave. I don't want you to,"

Castiel's gaze was intense. "How can we work this out, Dean? Tell me," When Dean was silent, Cas spoke again. "Exactly. We can't. If we continue to be friends things are going to get awkward,"

"You don't get it, Cas. I don't want to be friends," Dean said, quickly finishing his thought when a hurt expression came across the Angel's face. "I want to be more than friends, Cas! I want to work this out,"

"And what if it goes wrong, Dean?" Cas asked, his eyes shining. "What happens when you realize you're making a mistake and leave me? Our friendship will be over. You would never talk to me again,"

"Cas, Cas listen to me," Dean said softly as Cas tried to hold back his tears. "I love you, and I'm sorry I didn't tell you earlier. I was an asshole, and I should have let you know instead of pushing you away. Even if it doesn't work out, I would never leave you. I promise,"

"Do...do you really mean that...?" Cas asked, hope in his wavering voice.

"Of course," Dean replied, "of course I mean it. So...do you want to be in a relationship with me?"

Castiel stared at him in disbelief before nodding his head, a smile spreading on his face. "Yes," he said, now grinning at Dean.

Dean smiled back and grabbed his hand, squeezing it tightly. "Do you forgive me?" He asked.

Cas stared at him for a moment before suddenly pulling him close and kissing him. Dean was shocked for a moment, but slowly closed his eyes and melted into it. The hand that wasn't in Cas's was running through the Angel's hair. Cas's other hand was on Dean's back. The two kissed for what seemed like forever until finally Cas pulled away. "Does that answer your question?" He asked, a breathy laugh passing his lips.

Dean chuckled and pecked his cheek. "Come on," he said, leading Cas out of the room. "Let's go tell our brothers,"

Before they could leave, however, Cas stopped him and whispered something in his ear. Dean blushed as his heart raced before he started grinning. "I'll be right back," he said, leaving the room in a hurry.

* * *

"Do you think we did the right thing?"

Gabriel looked up at the worried, pacing Sam. "What do you mean?" he asked.

"Forcing Cas and Dean into this," Sam sighed, "look, I liked what we were doing at the time but...some part of me says they should have worked it out themselves,"

"They _did_ work it out themselves, Sammy," Gabriel said, "we just helped them along,"

Sam shook his head. "Then why are they just down the hall on the brink of a fight?"

"Because sometimes that's how love is," Gabriel shrugged, "I have never heard of one couple that has never gotten in an argument with each other,"

"I guess you're right,"

"Oh, I _am_ right,"

A few moments passed with nothing to be heard down the hall. Sam finally sat down, leaning back into a chair next to Gabriel. The kitten Castiel had dreamed up sleepily padded into the room and fell over at Sam's feet.

"Aww, Bumblebee," Gabriel cooed, leaning over and scratching the kitten's head.

"You named the cat _Bumblebee_?"

"No, I'd never name a cat Bumblebee," At Sam's confused look, Gabe explained. "Cassie named him. The kid just really likes bees. He wouldn't accept any other name,"

Sam was about to make a comment about it when all of a sudden Dean was poking his head out at them from behind the wall. There was a mischievous smirk on his face. "Uh, I gotta tell you guys something,"

"Shoot," Sam said, a smile on his face. He already had an idea of what that something was.

"I talked to Cas and...we're all good now," Dean smiled, "we're uh...together now so uh...thank you,"

Sam and Gabriel secretly high-fived each other between the chairs they were sitting in. Sam felt Gabriel grab his hand before he hurriedly pulled away. Sam decided to ignore it, thinking he was just imagining things. "Well congrats you guys. I'm really happy for-"

"Dean, hurry up!"

Sam and Gabriel exchanged terrified looks as Castiel's head and shoulders popped out from behind Dean. It looked like he was only wearing his trench coat and his tie. They watched in almost horror as Cas pulled Dean away from the room and down the hall. The door slammed shut, causing Bumblebee to jump awake. Sam picked up the small kitten and pet him soothingly, trying to forget what he just saw, and not thinking about what Cas and his brother were doing.

Suddenly, Gabriel muttered something in Enochian and covered his ears. Sam was about to ask him if he was okay when he started hearing noises coming from the room Dean and Cas were in. Sam's eyes widened and he stood, cradling Bumblebee in his arms and leaving the living room.

"Why don't we go downstairs," Gabriel said, snapping his fingers.

The downstairs living room was much different from the one upstairs. It had a TV, a large leather sofa in front of it, and a neat glass coffee table. Gabriel switched on the TV in hopes of drowning out the noise from upstairs. Unfortunately, Angels had much better hearing than humans, and Sam spent a lot of the time comforting a very traumatized Gabe.

After about an hour, Gabriel finally relaxed and sat up, sighing in relief. He only had a moment of comfort before his eyes widened in horror. "R-round two," he whispered.

Sam bit back a laugh and turned the TV up to 50, disturbing Bumblebee and hurting his hearing. Gabriel couldn't hear the two lovebirds upstairs, so Sam tolerated it. After all, just the thought of Dean and Cas having sex was disturbing to him, actually hearing it would scar him for life.

"Well, at least they're together," Sam finally said.

Gabriel just glared at him and curled up next to him, feeling miserable, but also secretly pleased that he could be this close to Sam.


	7. What About Us?

**What About Us?**

The next morning, Sam stumbled up the stairs and into the kitchen of Gabriel's house, the Arch-Angel right behind him. They both felt sluggish and tired, Sam not getting any sleep that night and Gabriel still traumatized due to Dean and Castiel's... _activities_. Although disturbed, Sam was actually surprised that his brother and the Angel had sex literally all night. And although it made him feel strange to admit it, but he was impressed with how long his older brother had last-

He decided to stop thinking about it.

When Sam and Gabriel entered the kitchen, they were both surprised to find Dean making bacon and pancakes. Cas was hovering around him, watching intently as Dean showed him how to make them. Dean flipped a pancake in the air, only to have it land right on his head. Castiel laughed loudly as the pancake slowly slipped down Dean's face. Dean caught it with his mouth before it completely fell off of his face. He ate it and winked at Cas, who was still laughing, albeit a little quieter. They didn't notice Sam and Gabriel in the room until Gabe coughed loudly.

"Oh, hey guys," Dean greeted them as they took seats beside each other at the table. "You two look tired. Not sleep well?"

Sam and Gabriel both gave him death glares, staring at him until he started chuckling. Cas put two plates with pancakes and bacon on them in front of them. Out of thin air appeared a mason jar filled with syrup. "I made it last night," Cas glanced over at Dean, "after Dean passed out only twelve hours into intercourse," He paused as Sam started coughing, "but then we started right back up again after a whole hour. I'm glad I gave him some strength because he wouldn't even be able to move today-"

"Cas," Dean said, gesturing for him to stop.

"Oh, my apologies,"

Sam pushed his plate away and awkwardly looked over at Gabriel, who had simply face planted in to his breakfast. Sam looked over at Cas and Dean and gave them his biggest bitch face. "Gabe had to listen to you two all night, y'know," he rubbed Gabriel's back, "he doesn't need a reminder of what happened,"

Dean and Cas exchanged looks before they shrugged and put the frying pan in the sink. "He had opportunities to leave," Dean said, "so it's only his fault,"

Gabe slowly lifted his head and glared at Dean, snapping his fingers. "Now the next time you two do it, Cas won't even be able to find your... _friend_ ,"

"What friend?" Cas asked, confusion etched across his face.

"The one that was inside of you last night," Gabriel deadpanned. Sam coughed and grabbed Gabriel's arm, slowly standing up with him and gently urging him out of the room.

"Shit is he serious?"

"I'm not sure. We should check,"

Gabriel stopped dead in his tracks as they overheard Dean and Cas talking. He snapped his fingers again and they disappeared, reappearing in a kitchen inside of a nice, small cottage on a beautiful lake. He sighed in relief, walking over to the fridge and pulling out two beer. Sam shook his head when he was offered one, thanking the Angel anyway. Gabriel shrugged and chugged his bottle before moving on to Sam's.

"You look like Death, Sammy," Gabriel commented, "you should go sleep,"

Sam yawned, suddenly feeling very tired. "Yeah, I am pretty beat," he admitted.

"Bedroom's down the hall. Doesn't matter which one you sleep in," Gabriel murmured, grabbing more alcohol.

"Are you...getting yourself drunk...?"

Gabriel merely nodded his head and downed another bottle of beer. Sam laughed slightly and shook his head, leaving the room and walking down the hall. He opened a door to find a very nice room with a large bed in the middle of it. Sam took off his shoes and jacket before falling on to the bed and instantly going to sleep.

* * *

Gabriel's feelings for Sam had invaded nearly every part of his mind now. When he thought of candy, he instantly thought of Sam giving him candy. When he thought of alcohol, he thought of drinking it with Sam. When he thought of sex - well, you get the picture.

The point was, Gabriel had become a slave to his feelings for Sam, and every fibre of his being wanted to be with Sam. Surely the hunter knew this, but did he feel the same? There was only one way to find out, and he didn't think he could do it sober. Once he could feel a buzz, which took about two hours, he stumbled into the room Sam was sleeping in and watched him from the doorway for awhile. He had to say, humans were such cute creatures. Especially when they were asleep.

Gabe stumbled over to Sam and kneeled in front of the human. He studied his sleeping face closely, frowning when a crease formed on his forehead. Gabriel ghosted his fingers over it, smoothing it and taking away any possibility of a bad dream. He sighed, sitting cross legged on the floor. He took Sam's hand, which was flung over the side of the bed.

"You must have been pretty tired," Gabriel whispered, slurring his words slightly. "I should have popped us over hear earlier but...truthfully, I really enjoyed being...near you last night,"

Sam's face was still peaceful, no signs of waking up. Gabe chuckled, gently rubbing his thumb over Sam's knuckles. "I'm _soooo_ drunk right now," Gabriel admitted, "and now I'm going to get even more drunk so I can ask you if you love me," He shakily stood and placed a small kiss on Sam's forehead before stumbling back out of the room and quietly shutting the door.

Little did he know, Sam had been awake through all of it, and he smiled tenderly when Gabriel left. Sam didn't want the Angel to get alcohol poisoning (even though Angels probably couldn't), so he got out of bed and walked into the kitchen, pretending that he had just woke up seconds ago. "Christ, Gabe," Sam muttered, "how drunk do you plan on getting?"

Gabriel turned around, smiling sloppily at the sight of Sam. " _Very_ drunk," he replied.

Sam sighed and gently took the bottle in Gabriel's hand away from him. "Gabe, it's okay,"

"Wha's okay?"

"I know what you're going to ask me already,"

Gabriel swallowed and looked away. "And...?"

"And I feel the same," Sam said, putting the bottle down and cupping his Angel's face in his hands. "I love you too, Gabe,"

Gabriel absolutely beamed. He jumped and threw his arms around Sam. "Thanks, Samsquatch,"

Sam chuckled at the nickname and rubbed his back. He put him back on the ground and kissed the top of his head. "Thank _you_ , Gabriel,"

Gabe smiled and snapped his fingers. The bottles of liquor were gone and they were standing in the kitchen of Gabriel's actual house. They heard chaos just down the hall and ran over to see Cas standing in front of a door.

"Dean, body parts don't even matter," Cas whined, "I still love you,"

"I'm... _memberless,_ Cas!" Deans muffled voice yelled from behind the door.

Cas sighed and turned to face Sam and Gabriel, who were holding hands. He nodded his head approvingly at them before shaking his head and donning an angry expression on his face. "Fix this, Gabriel," his voice was commanding, like how Sam imagined him as a leader in Heaven.

Gabe rolled his eyes and snapped his fingers, giving Cas a mock smile as Dean cried out in relief. He opened the door and glared at Gabriel as he did up his jeans. "Don't ever do that to me again," he growled. His expression softened when Cas grabbed on to Dean's arm to calm him. Dean glanced over at him and smiled, looking happier than Sam had ever seen him. He couldn't help but smile too. His brother really was in love.

"Um _hellooo_ ," Gabe said, raising his and Sam's tightly clasped hands. "Isn't anyone gonna congratulate us?"

Sam felt heat gush over his cheeks as Dean looked them over. "Hurt my brother and I kill you," He grumbled at Gabriel. Sam made a small sound of annoyance when Gabriel's posture stiffened.

"Likewise," He replied, a glare on his face.

"Okay! Why don't we go downstairs and watch a movie!" Sam exclaimed, quickly changing the subject.

"Yes that sounds like a brilliant idea," Cas chimed in, glancing over at Dean.

"Fine," their brothers muttered in unison.

Sam and Gabriel got to pick the movie, since they were the 'newest couple'. Gabriel didn't know what to watch, so Sam flicked through channels until he found a movie that looked interesting.

"Oh this is that Angel movie with Paul Bettany in it," Dean instantly recognized it, watching intently despite Cas's conflicted expression.

The rest of the movie consisted of Gabriel and Cas pointing out all of the various errors in the movie. They yelled out things like, "Micheal isn't that good looking!" and when 'Gabriel' appeared on screen, the real Gabriel merely snorted in amusement. Instead of this annoying the Winchesters however, the brothers found it adorable, and they only appreciated the Angels' company more.

* * *

 **The movie I'm referring to is called Legion :)**


	8. Finale

**Thanks so much to everyone who read, favourited, followed, and reviewed :) You guys really make my day ^-^**

 **Special thanks to DemigodPrefect for reviewing almost every chapter :)**

 **Thanks for sticking around and I hope you like the ending!**

* * *

 **Finale**

When Sam and Gabriel first started the challenge, they had no idea how long it would take for it to finish. They had no idea if it would even work. It was just a fun way to get two people who love each other together. Looking back, they were both extremely glad they did it. Even though technically the contest ended before Dean and Cas got together, it had been even more than a complete success.

Getting Castiel and Dean together had certainly changed their lives for the better. Dean became a kinder, gentler person, Castiel became better at his 'people skills', and Sam and Gabriel learned to love each other more deeply than ever before. The four of them were a brilliant family. Castiel and Dean specialized in the action aspect of hunting, whereas Gabriel and Sam were the best there was at research (it also helped that Gabriel was an Arch-Angel). Together, the four of them made a perfect team. Demons and monsters didn't have a chance against them.

It had been about a year after the couples had got together. The hunting business was dying down and the group could actually relax for awhile in between hunts. During one of their days off, Gabriel pulled Cas to the side, saying they had to have a brotherly talk. Sam and Dean thought nothing of it, continuing to drink and watch the Lord of the Rings marathon that was on TV. What they didn't know was that Gabriel and Cas were planning something.

The next day, Gabriel walked into the kitchen where the two sleepy Winchester brothers were drinking coffee. He grinned at them. "Cassie and I are going shopping," he said, "we'll be back soon,"

"Wait, why are you guys going?" Sam asked, seeming wary.

"I want new clothing," Castiel said, scaring everyone but Dean as he randomly appeared into the room. Sam and Dean glanced at each other as Gabriel nodded enthusiastically.

Sam was about to comment further when suddenly, the angels were gone.

* * *

Cas and Gabriel appeared in the middle of a mall in front of a jewelry store. Cas stared at it in almost awe and Gabriel had to pull him into the store. When they were inside, the two of them awkwardly looked around, trying not to knock anything over with their wings. The store was pretty much empty except for them. It was surprising, for Castiel found some of the items very beautiful. From earrings to anklets, they were quite stunning. He was pulled from his awe when finally, Gabriel called his brother over.

"What d'you think?" Gabe asked, pointing. "Do you think they'd like them?"

Cas found himself smiling. "They'll love them, I'm sure of it,"

Once they bought what they had came for, Cas and Gabriel took a look around the mall. Gabriel bought a plaid shirt for himself that reminded him of Sam's, and Cas ended up buying a band tee with the logo of a band Dean had shown Cas. Gabriel found a very large stuffed moose and bought it for Sam. Cas could only find a CD, and he hoped Dean would forgive him for such a small gift. When they were finished, the Angels zapped back to the house, careful to hide what they bought at the jewelry store before announcing their return.

"Sammy! I bought something for ya!" Gabriel yelled.

Castiel smiled in amusement as Sam walked into the room and started laughing at the large stuffed moose. "Wow, that's amazing, Gabe!" He exclaimed. Gabriel beamed and they exchanged a small kiss before Dean walked into the room. He eyed the moose wearily before walking over to Cas and giving him a kiss hello.

"I got you something too, Dean," Cas said softly after pulling away. "Forgive me, I couldn't find something as big as the moose,"

Dean shook his head and smiled as Cas pulled the CD of classic rock hits out of his coat. Dean snatched it out of his hands, exclaiming something about how all of his favourite bands were on it. Cas was surprised when Dean hugged him tightly, thanking him. Cas put his arms around him knowing that Dean couldn't feel his wings embracing him.

The tender moment was broken when Gabriel loudly announced that he was hungry and the Winchesters ordered a pizza in response.

* * *

Now, a week later, Dean and Sam found themselves in a beautiful park, reading over clues their boyfriends had given them.

"They've gotta be somewhere around here!"Sam exclaimed, looking around. Dean ignored him and looked over towards the gazebo area of the park. He tapped Sam to get his attention and pointed to the gazebo. Before their eyes, Castiel and Gabriel appeared inside of it, dressed up very nicely and hands behind their backs. Sam and Dean hurriedly walked over, stopping in front of the gazebo.

Cas and Gabe exchanged looks before Cas nodded his head and dropped on one knee in front of Dean.

"Dean,"

Gabe did the same, dropping in front of Sam.

"Sam,"

They showed the engagement rings to their partners.

"Will you marry me?" They asked in unison.


End file.
